Organic light-emitting device and electronic apparatus including the same
Abstract
An organic light-emitting device and an electronic apparatus including the same are provided. The organic light-emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer provided between the first electrode and the second electrode and including an emission layer, wherein the emission layer includes a first compound that is a hole-transporting compound, a second compound that is an electron-transporting compound, a third compound capable of emitting phosphorescence, and a fourth compound capable of emitting delayed fluorescence, and a value of R 0 is at least 3.5 nm.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An organic light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; and an interlayer arranged between the first electrode and the second electrode and comprising an emission layer, wherein the emission layer comprises a first compound that is a hole-transporting compound, a second compound that is an electron-transporting compound, a third compound configured to emit phosphorescence, and a fourth compound configured to emit delayed fluorescence, the first compound, the second compound, the third compound, and the fourth compound are different from each other, and a value of R 0 calculated according to Equation 1 is at least 3.5 nanometer (nm), and
R
0
=
9000
(
ln
10
)
κ
2
Q
D
128
π
5
N
A
n
4
J
Equation
1
wherein, in Equation 1,
κ 2 is a dipole orientation factor between the third compound and the fourth compound, Q D is a quantum yield of the third compound, NA is an Avogadro constant, n is a refractive index of a medium, and J is an overlapping area of a light-emitting area of the third compound and a light-absorption area of the fourth compound.
2 . The organic light-emitting device of claim 1 , wherein
a value of R 0 is at least 3.5 nm and at most 5.5 nm.
3 . The organic light-emitting device of claim 1 , wherein
the first compound and the second compound form an exciplex.
4 . The organic light-emitting device of claim 1 , wherein
a ratio of light to be emitted from the fourth compound, with respect to total light to be emitted from the emission layer, is at least 50%.
5 . The organic light-emitting device of claim 1 , wherein
the first compound comprises: two carbazole groups; one carbazole group and one dibenzofuran group; or a benzene group and/or a Si atom.
6 . The organic light-emitting device of claim 1 , wherein
the first compound comprises a compound represented by Formula 1:
and
wherein, in Formula 1, ring A 11 and ring A 12 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
L 11 is a single bond, a C 6 -C 30 carbocyclic group that is unsubstituted or substituted with R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
n11 is an integer from 1 to 5,
Ar 11 is a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with R 10a , a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with R 10a , —C(Q 1 )(Q 2 )(Q 3 ), or —Si(Q 1 )(Q 2 )(Q 3 ),
R 11 and R 12 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
b11 and b12 are each independently an integer from 1 to 10,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(O 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, or a combination thereof; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, —Si(Ph) 3 , or a combination thereof.
7 . The organic light-emitting device of claim 1 , wherein
the second compound comprises a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a combination thereof.
8 . The organic light-emitting device of claim 1 , wherein
the second compound comprises a compound represented by Formula 2:
and
wherein, in Formula 2,
X 21 is C(R 24 ) or N, X 22 is C(R 25 ) or N, X 23 is C(R 26 ) or N, and at least one of X 21 to X 23 is N,
L 21 to L 23 are each independently a single bond, a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with R 10a , or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with R 10a ,
n21 to n23 are each independently an integer from 1 to 5,
R 21 to R 26 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(O 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —CI; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, or a combination thereof; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, —Si(Ph) 3 , or a combination thereof.
9 . The organic light-emitting device of claim 1 , wherein
the third compound comprises platinum (Pt).
10 . The organic light-emitting device of claim 1 , wherein
a difference between a triplet energy level (eV) of the fourth compound and a singlet energy level (eV) of the fourth compound is at most 0.5 eV.
11 . The organic light-emitting device of claim 1 , wherein
the fourth compound comprises boron (B).
12 . An organic light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; and an interlayer arranged between the first electrode and the second electrode and comprising an emission layer, wherein, the emission layer comprises a first compound as a hole-transporting compound, a second compound as an electron-transporting compound, a third compound represented by Formula 3, and a fourth compound, the fourth compound comprises a C 8 -C 60 polycyclic group-containing compound comprising at least two condensed cyclic groups that share a boron atom (B), the first compound, the second compound, the third compound, and the fourth compound are different from each other, and a value of R 0 calculated according to Equation 1 is at least 3.5 nm,
wherein, in Formula 3,
M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm),
X 31 to X 34 are each independently C or N,
ring CY 31 to ring CY 34 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, and
L 31 to L 33 are each independently a single bond, *—C(R 3a )(R 3b )—*′, *—C(R 3a )═*′, *═C(R 3a )—*′, *—C(R 3a )═C(R 3b )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*, *—B(R 3a )—*′, *—N(R 3a )—*′, *—O—*′, *—P(R 3a )—*′, *—Si(R 3a )(R 3b )—*′, *—P(═O)(R 3a )—*′, *—S—*′, *—S(═O)—*′, *—S(═O) 2 —*′ or *—Ge(R 3a )(R 3b )—*′, and * and *′ each indicate a binding site to a neighboring atom,
n31 to n33 are each independently an integer from 1 to 5,
R 31 to R 34 , and R 3a and R 3b are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
R 3a and R 3b are optionally bonded to each other to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a , b 31 to b 34 are each independently an integer from 0 to 10,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —CI; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, or a combination thereof; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, —Si(Ph) 3 , or a combination thereof, and
R
0
=
9000
(
ln
10
)
κ
2
Q
D
128
π
5
N
A
n
4
J
Equation
1
wherein, in Equation 1,
κ 2 is a dipole orientation factor between the third compound and the fourth compound, Q D is a quantum yield of the third compound, NA is an Avogadro constant, n is a refractive index, and J is an overlapping area of a light-emitting area of the third compound and a light-absorption area of the fourth compound.
13 . The organic light-emitting device of claim 12 , wherein
the fourth compound comprises a compound represented by Formula 4-1 or 4-2:
wherein, in Formulae 4-1 and 4-2,
ring A 41 to ring A 45 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
X 41 is O, S, N(R 46 ), B(R 46 ), C(R 46a )(R 46b ), or Si(R 46a )(R 46b ),
X 42 is O, S, N(R 47 ), B(R 47 ), C(R 47a )(R 47b ), or Si(R 47a )(R 47b ),
X 43 is O, S, N(R 48 ), B(R 48 ), C(R 48a )(R 48b ), or Si(R 48a )(R 48b ),
X 44 is O, S, N(R 49 ), B(R 49 ), C(R 49a )(R 49b ), or Si(R 49a )(R 49b ),
R 41 to R 49 , R 40a , R 46a , R 47a , R 48a , R 49a , R 40b , R 46b , R 47b , R 48b , and R 49b are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
b41 to b45 are each independently an integer from 1 to 10, and
R 10a and Q 1 to Q 3 are each as those described in Formula 3.
14 . The organic light-emitting device of claim 12 , wherein:
the second compound comprises a compound represented by Formula 2-1 or Formula 2-2:
wherein, in Formulae 2-1 and 2-2,
X 21 is C(R 24 ) or N, X 22 is C(R 25 ) or N, X 23 is C(R 26 ) or N, and at least one of X 21 to X 23 is N,
L 22 and L 23 are each independently a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
n22 and n23 are each independently an integer from 1 to 5,
R 22 , R 23 , Z 21 , Z 23 , Z 24 , and Q 1a to Q 3a are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
c21 and c22 are each independently an integer from 1 to 3,
c23 and c24 are each independently an integer from 1 to 4, and
R 10a and Q 1 to Q 3 are each the same as those described in Formula 3.
15 . The organic light-emitting device of claim 1 , wherein
the emission layer is configured to emit blue light.
16 . The organic light-emitting device of claim 1 , wherein
the first electrode is an anode, the second electrode is a cathode, the interlayer comprises a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode, the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron-blocking layer, or a combination thereof, and the electron transport region comprises a buffer layer, a hole-blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a combination thereof.
17 . An electronic apparatus comprising the organic light-emitting device of claim 1 .
18 . The electronic apparatus of claim 17 , further comprising
a thin-film transistor, wherein the thin-film transistor comprises a source electrode and a drain electrode, and the first electrode of the organic light-emitting device is electrically connected to the source electrode or to the drain electrode of the thin-film transistor.
19 . A consumer product comprising the organic light-emitting device of claim 1 .
20 . The consumer product of claim 19 , being at least one selected from among
a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, a signboard, and combinations thereof.Join the waitlist — get patent alerts
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